Tetrabutylammonium Fluoride → HCID 18332419, compound

HRID 2268788Notes

Reaction equation

HRID 2268788 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[F:19][C:20]1[CH:28]=[C:27]2[C:23]([C:24]([C:29]3[CH2:30][CH2:31][N:32]([CH2:35][CH2:36][N:37]4[C:42]5[CH:43]=[CH:44][C:45]([CH2:47][O:48][Si](C(C)(C)C)(C)C)=[CH:46][C:41]=5[CH2:40][N:39]([CH:56]([CH3:58])[CH3:57])[S:38]4(=[O:60])=[O:59])[CH2:33][CH:34]=3)=[CH:25][NH:26]2)=[CH:22][CH:21]=1>C1COCC1>[F:19][C:20]1[CH:28]=[C:27]2[C:23]([C:24]([C:29]3[CH2:34][CH2:33][N:32]([CH2:35][CH2:36][N:37]4[C:42]5[CH:43]=[CH:44][C:45]([CH2:47][OH:48])=[CH:46][C:41]=5[CH2:40][N:39]([CH:56]([CH3:57])[CH3:58])[S:38]4(=[O:59])=[O:60])[CH2:31][CH:30]=3)=[CH:25][NH:26]2)=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 69950506HCID 69950506, compound

Product 1

HCID 18332419HCID 18332419, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Tetrabutylammonium fluoride (2 ml, 0.002 mol, 1M in THF) was added to a suspension of 1-[2-[4-(6-fluoro-1H-indol-3-yl)-3,6-dihydro-1(2H)-pyridinyl]ethyl]-6-t-butyldimethylsiloxymethyl-3,4-dihydro-3-(1-methylethyl)-1H-2,1,3-benzothiadiazine-2,2-dioxide (1.1 g, 0.0018 mol) in THF (18 ml) under argon then stirred at room temperature for 2 h, evaporated to dryness and purified by flash chromatography using dichlormethane/methanol (97:3) as eluent, to give 1-[2-[4-(6-fluoro-1H-indol-3-yl)-3,6-dihydro-1(2H)-pyridinyl]ethyl]-3,4-dihydro-6-hydroxymethyl-3-(1-methylethyl)-1H-2,1,3-benzothiadiazine-2,2-dioxide as a pale yellow solid. Mp: 113-115° C. 1H-NMR (CDCl3, 300 Mz), δ: 8.09 (NH, s), 7.76 (1H, dd), 7.22 (1H, d), 7.11 (1H, d), 7.08 (1H, s), 7.01 (1H, dd), 6.98 (1H, d), 6.88 (1H, dt), 6.13 (1H, t), 3.29 (2H, s), 2.85-2.81 (4H, m), 2.58 (2H, s), 1.11 (6H, d).

Workup

  1. customevaporated to dryness
  2. custompurified by flash chromatography

Sources & evidence

ORD record
ord-5722dcb195dc427f9c53283cbe68c217
Source dataset
uspto-grants-2001_12
Patent number
US06329366B1

Reaction notes

Loading…